Synthesis of novel L-2′,3′-dideoxy-2′-trifluoromethyl-4′-thiocytidines from α-trifluoromethyl-α,β-unsaturated ester

被引：25
|
作者：
Zhang, XG
Qing, FL
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Donghua Univ, China & Coll Chem & Chem Engn, Shanghai 200051, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 03期
关键词：
D O I：
10.1021/jo0159690
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short and efficient synthesis of L-2',3'-dideoxy-2 -trifluoromethyl-4'-thiocytidines is described. (2R,4S/2S,4S)5-(tert-Butyldimethylsiloxy)-2-trifluoromethylpentan-4- olide (3a and 3b) are prepared from alpha-trifluoromethyl-alpha,beta-unsaturated ester (1) in three steps and converted to compounds 6a and 6b. The corresponding 1-O-acetyl derivatives 8a and 8b were obtained via the usual Pummerer rearrangement from 6a and 6b in two steps, which were in turn used to synthesize L-4'-thiocytidines 10a and 10b.
引用
收藏
页码：1016 / 1019
页数：4
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